1-Halopyrazin- and 1-halopyrimidin-4-amino-4-alkylpiperidines

Abstract

The present invention relates to novel heteroarylpiperidines of formula (I): ##STR1## in which Hal is a halogen atom, Alk is a C 1-4 alkyl group and one of X, Y and Z is a nitrogen atom while the others are ═CH--, and their salts. These compounds are useful as 5-HT 3 agonists.

What is claimed is: 
     
       1. A compound of formula (I): ##STR12## in which Hal is a halogen atom, Alk is a (C 1  -C 4 )alkyl group and one of X, and Z is a nitrogen atom and the others are --CH═, and its pharmaceutically acceptable or unacceptable salts. 
     
     
       2. A compound of formula (I) according to claim 1 in which Alk is a methyl group and Hal is a chlorine atom, or one of its pharmaceutically acceptable or unacceptable salts. 
     
     
       3. A compound as claimed in claim 1 which is 4-Amino-1-(4-chloropyrimidin-2-yl)-4-methylpiperidine and its pharmaceutically acceptable salts. 
     
     
       4. A compound as claimed in claim 1 which is 4-Amino-1-(4-chloropyrimidin-2-yl)-4-methylpiperidine maleate. 
     
     
       5. A compound as claimed in claim 1 which in 4-Amino-1-(2-chloropyrimidin-4-yl)-4-methylpiperidine and its pharmaceutically acceptable salts. 
     
     
       6. A compound as claimed in claim 1 which is 4-Amino-1-(2-chloropyrimidin-4-yl)-4-methylpiperidine maleate. 
     
     
       7. A method for inducing a serotoninergic agonist action on 5HT 3  receptors of a mammal which comprises administering to said mammal an effective amount of at least one compound of formula (I): ##STR13## in which Hal is a halogen atom, Alk is a (C 1  -C 4 )alkyl group, and one of X, and Z is a nitrogen atom and the others are --CH═, or one of its pharmaceutically acceptable salts. 
     
     
       8. A pharmaceutical composition for inducing a serotoninergic agonist action on 5HT 3  receptors of a mammal, wherein the composition contains an effective amount of a compound of formula (I) as claimed in claim 1: ##STR14## in which Hal is a halogen atom, Alk is a (C 1  -C 4 )alkyl group and one of X, and Z is a nitrogen atom and the others are --CH═, or one of its pharmaceutically acceptable salts, is present as the active principle. 
     
     
       9. A pharmaceutical composition according to claim 8 in which a compound of formula (I) in which Hal is a chlorine atom and Alk is a methyl group, or one of its pharmaceutically acceptable salts, is present as the active principle. 
     
     
       10. A pharmaceutical composition in which a compound according to claim 3 is present as the active principle. 
     
     
       11. A pharmaceutical composition in which a compound according to claim 5 is present as the active principle. 
     
     
       12. A method according to claim 7 for the treatment and/or prophylaxis of dysthymic disorders, psychotic disorders, cases of anxiety or intestinal motivity disorders such as constipation or IBS. 
     
     
       13. A method as claimed in claim 7 wherein the compound of formula (I) is 4-amino-1-(4-chloropyrimidin-2-yl)-4-methylpiperidine or a pharmaceutically acceptable salt thereof. 
     
     
       14. A method as claimed in claim 7 wherein the compound of formula (I) is 4-amino-1-(4-chloropyrimidin-2-yl)-4-methylpiperidine maleate. 
     
     
       15. A method as claimed in claim 7 wherein the compound of formula (I) is 4-amino-1-(2-chloropyrimidin-4-yl)-4-methylpiperidine or a pharmaceutically acceptable salt thereof. 
     
     
       16. A method as claimed in claim 7 wherein the compound of formula (I) is 4-amino-1-(2-chloropyrimidin-4-yl)-4-methylpiperidine maleate.